The largest city in Maine, Portland is a cultural gem whether you prefer the classics — the rapidly expanding collection at its art museum features the likes of Warhol and Monet — or something a little more offbeat — its International Cryptozoology Museum claims to have Bigfoot and Abominable Snowman hair samples on display. One respondent to Money’s reader poll calls Portland “a foodie heaven,” with standout restaurants including Hot Suppa (Southern food), Central Provisions (small plates), Scales (seafood) and HiFi Donuts (… doughnuts).

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Boats docked in Portland, Maine
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Nature lovers will feel right at home in Portland. Not only is its downtown extremely walkable, but as the survey respondent notes, “within a short distance, you can enjoy mountains, water sports, the ocean, clean lakes and other amenities.” Clean lakes is no exaggeration: Portland is famous for its high-quality tap water, courtesy of Sebago Lake.

Even the city’s paved spaces are thriving. Thanks in part to a revitalization project in 2015, Congress Square Park has become a bustling hub with free Wi-Fi, outdoor furniture and a full roster of events like silent-movie showings and the Queer Makers Market.

People walking in Portland's Art District
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Portland is an unapologetically hip pocket of the Pine Tree State, but it’s also a great place for families. Portland High School (founded in 1821!) won a GreatSchools award in 2022 for its emphasis on preparing students for college. Though houses tend to be expensive, the city is chock-full of kid-friendly venues like Bug Light Park, a popular picnic and kite-flying spot. In the summer, Palace Playland — a massive beachfront amusement park — is just a 30-minute drive away.